What is Straight to Gay?

Hi! I’m Amy, and welcome to my misadventures as a Generation X lesbian. It’s been quite a ride over these past two decades!

Like most LGBTQ women of my generation, I didn’t always date women. I was married to a man, and had exclusively dated men prior. And I was good at heterosexual dating—it was, in retrospect, so much easier. Remember Samantha from Sex and the City famously saying, “Men aren’t that complicated. They’re kind of like plants.”?  Well relationships with women ARE complicated, layered and complex—as one gay friend put it, you can’t dial it in with lesbians! But once I was with a woman, I never went back. And you’re about to learn why!

We’ll also explore why even as the younger generations are totally at ease with concepts like gender fluidity, Gen X seems stuck in a time warp. So much progress has been made on LGBTQ rights and visibility since I came out two decades ago, and yet the journey and struggles to live as one’s authentic self continues for women of my generation. Why is this? 

This might disappoint some of you, but I never kiss and tell. I’ve dated famous women—some who are out, others not—and scores of others who have shaped my journey and experiences.  I’ll be fictionalizing aspects of each woman I write about to hide her identity.  It’s not about her, it’s about the lessons each taught me from our shared experiences.

On a happier note, I do plan lots of discussions about sex (because that is what most of you are here for, right? Kidding!) Not the male producer version of what he fantasizes lesbian sex to be—the actual sexual experience between two women, which is something I LOVE! I will also be keeping it real: writing about my joys and heartbreaks, my struggles and triumphs, and the innumerable lessons l have learned along the way. I promise to make you laugh and cry, learn and discover, evaluate and question—even need to leave the computer for a cold shower.

Finally, these are my stories. I don't presume to speak for the entire Gen X LGBTQ community—how could I?  These are my experiences and slice of life, which I share with some trepidation, but with the hope that my voice may give strength, comfort and validation to other Gen X women who are on, or considering starting, their journey. 

For subscribers ($5/month):

  • You’ll be emailed one “Straight to Gay” story each week

  • You'll have access to podcasts for every story

  • You’ll be admitted to an open-thread “Hangout” with me for extra access and questions about each story the next day.

Why Now?

A decade ago I was meeting with Esther, my editor, brainstorming two book ideas—both fun:  one about my adventures on Wall Street, and the other my journey from straight to gay. Each time we met, we’d ask the people seated nearby which book theme they’d be more interested in reading. Sure enough, without exception, they all wanted the straight to gay book. But at the time I was focused on my work with The New Agenda, a national women’s organization I co-founded, and career advice seemed a perfect fit, so we decided it was best to eat the broccoli first.

I was well along with the Wall Street book, and had started to meet with literary agents, when a personal tragedy struck: the loss of my second parent. My dad had been my biggest cheerleader, and was hoping to see the first book in print before he passed. After he died, I mourned, and lost my heart for writing. Years later, as my kids were heading off to college and finishing high school, I planned to get back to writing the two books after Hillary won the election. People plan, G-d laughs. 

I had always assumed, in the decade between, that others would write about the real struggles my generation was having with sexuality—and there were small bread crumbs, but I never felt seen. Until Season 2 of The Morning Show! With the interplay of Julianna Margulies and Reese Witherspoon, I felt described—FINALLY!—AT LAST! A portrayal of a woman my age who was forced out of the closet in the late 1990s then fired, in a burgeoning, current day relationship with a Gen X woman who was struggling to live as her authentic self. 

I looked at my own life.  Since I resumed in-person dating with Covid vaccines, the three women I had dated and been intimate with were all beautiful, Gen Xers; but none were out as gay. For two —including one well known actress—I was their first sexual experience with a woman, and the third was bisexual. All three had been married to men. The bisexual woman identified with Bradley (Reese’s character), coming from a Southern conservative state and feeling a certain amount of family shame around her sexuality. She saw me as a Laura figure (Julianna’s character)—someone with a high EQ who had already been on the journey and was a guide. Then came the Season 2 finale, and my disappointment of the showrunner entirely writing out Laura: a lapse that resonated with many LGBTQ women, who tweeted their displeasure at being erased and misunderstood.

So here I am, finally. To share my stories with the hope that other gay Gen X women will see themselves and feel validated. Others reading along might find the courage to live as their authentic selves. And the rest might have a better understanding of the Gen X LGBTQ women in your lives and our journeys.

Who am I?

I am a 55 year-old mother of two children and two very spoiled dogs. 

My life has had several chapters. I worked on Wall Street for two decades after college, and quickly climbed the ranks. At age 40, I retired to spend time raising my children, and shortly after, got involved with politics and Hillary Clinton’s historic 2008 run. After she lost, in reaction to the prevalent and disturbing sexism she faced, I co-founded The New Agenda, which I still lead today. I also became active on LGBTQ rights: writing and speaking on issues that impact our community. In November 2016, I found myself thrown into the very public spotlight as a sentinel for democracy, and spent the next four plus years chronicling broken norms and our near descent into authoritarianism, in a project called The Weekly List.

Being the glass half full person that I am, I assumed when President Joe Biden took office my chronicling work would be complete, and our democracy restored. When the Big Lie crystalized within the Republican Party, and Rep. Liz Cheney was kicked out of GOP leadership, I realized we were more likely in the third inning of our battle to defeat authoritarianism. So while I work to finalize archiving The Weekly List collection at the University of Pennsylvania’s Annenberg School, and continue activism for democracy ahead of the 2022 midterms, I am hoping this project can be the fun dessert to go along with the broccoli.

Subscribe to Straight to Gay

Activist and author Amy Siskind shares stories and lessons from her misadventures as a Generation X lesbian.


Activist, feminist and author. The Weekly List and podcast, archived at @AnnenbergPenn. Founder/President @TheNewAgenda. Former Wall Street executive. She/her. More at AmySiskind.com